Potassium Carbonate → HCID 68556375, Verbindung

HRID 2382104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382104
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH:16]=[CH2:17])[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1Cl)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16]([CH3:17])=[CH:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16](=[CH2:17])[CH2:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 2

HCID 11430Potassium CarbonateHCID 68557669Carbamic acid, N-(3-chloro-4-pyridinyl)-N-2-propen-1-yl-, 1,1-dimethylethyl ester

Produkt 2

HCID 68555346HCID 68555346, VerbindungHCID 68556375HCID 68556375, VerbindungAusbeute 117,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of allyl-(3-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (8.25 g, 30.8 mmol), tetrabutylammonium chloride (9.67 g, 30.8 mmol), palladium acetate (691 mg, 3.08 mmol) and potassium carbonate (12.8 g, 92.3 mmol) in DMF (100 mL) is heated at 800 C. for 1.5 h. The reaction is diluted with DCM and washed three times with water. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford a mixture 3-methyl-pyrrolo [3,2-c]pyridine-1-carboxylic acid tert-butyl ester and 3-methylene-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (4.21 g, total).

Aufarbeitung

  1. temperatureis heated at 800 C
  2. washwashed three times with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-3bd95e96910e4a518c80c917ada22c09
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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